Zwitterionic quaternary ammonium sulfonates and sulfates and lubricants and fuels containing same

ABSTRACT

Zwitterionic Quaternary ammonium sulfates, and sulfonates are provided as new compounds and as highly effective additives to lubricants and liquid fuels. They have a variety of desirable effects, among them being their ability to reduce friction in an internal combustion engine, thereby reducing the amount of fuel consumed.

This is a division of copending application Ser. No. 403,264, filed July29, 1982 now U.S. Pat. No. 4,536,309.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention is concerned with a novel group of compounds and their usein lubricants or liquid fuels as friction reducers, antioxidants andantiwear corrosivity reducers (i.e., non-corrosive to copper).

2. Discussion of the Related Art

It is known that sliding or rubbing metal or other solid surfaces aresubject to wear under conditions of extreme pressure. Wearing isparticularly acute in modern engines in which high temperatures andcontact pressures are prevalent. Under such conditions, severe erosionof metal surfaces can take place even with present generation lubricantsunless a load carrying or antiwear additive is present herein.

Friction is also a problem any time two surfaces are in sliding orrubbing contact. It is of special significance in an internal combustionengine and related power train components, because loss of a substantialamount of the theoretical mileage possible from a gallon of fuel istraceable directly to friction.

With respect to the novel compounds of this invention, no art is knownthat teaches or suggests them. Also, no art is known that teaches orsuggests the use of the instant compounds in a lubricant or fuel.

SUMMARY OF THE INVENTION

In accordance with the invention, there is provided a compound of theformula ##STR1## wherein (1) R is a C₁ to C₃₀, preferably a C₈ to C₃₀,hydrocarbyl group or is selected from the formulas ##STR2## wherein R⁴is a C₁ to C₃₀, preferably a C₇ to C₃₀, hydrocarbyl group, R⁵ ispreferably a C₂ to C₄ alkyl group and R⁶ is a hydrogen or methyl, (2) R¹and R² are C₁ to C₃₀, preferably methyl or a C₈ to C₃₀, hydrocarbylgroups, (3) R³ is benzyl or C₂ to C₆ alkylene group and, (4) Q is asulfonate or sulfate group.

The invention also provides a lubricant or liquid hydrocarbon fuelcomposition comprising a lubricant or fuel and a friction reducing orantiwear amount of the product. It is further contemplated that theproduct will aid in the reduction of fuel consumption in an internalcombustion engine.

DESCRIPTION OF SPECIFIC EMBODIMENTS

The compounds of this invention can be made by methods generally knownto the prior art. In general the sulfonates can be made by reacting theappropriate ammonium halide with, e.g., chlorosulfonic acid and thesulfates of the invention can be made by reacting the appropriate amineor amidoamine with, e.g., a chloroalkyl sulfate such in accordance withthe following illustrative reactions: ##STR3##

The chlorosulfonic acid is readily available commercially and itspreparation is well known. The sulfates are generally available also,but a useful sulfate can be prepared by reacting chlorobutanol andchlorosulfonic acid set forth herein below.

The reaction between the ammonium halide and chlorosulfonic acid can becarried out at from about 20° C. to about 90° C., preferably from about25° C. to 60° C. The reaction between the amine and sulfate can becarried out at from about 80° C. to about 140° C., preferably from about90° C. to about 120° C. The temperature chosen will depend to someextent on the particular reactants and on whether or not a solvent isused. In carrying out the reactions, it is preferable that quantities ofreactants be chosen such that the ratio of ammonium halide, amine oramidoamine to the sulfating or sulfonating agent is from about 1:4 toabout 1:1, preferably about 1:2 to about 1:1.

While atmospheric pressure is generally preferred, the reaction can beadvantageously run at from about 1 to about 5 atmospheres. Furthermore,where conditions warrant it, a solvent is preferred. In general, anyrelatively unreactive solvent can be used, including ethylenedichloride, and chloroform.

The times for the reactions are not critical. Thus, any phase of theprocess can be carried out in from about 1 to about 50 hours.

In the above formulas, "hydrocarbyl," includes alkyl, alkenyl, aryl,aralkyl and alkaryl groups. These specifically include, but are notlimited to, alkyl groups of from 1 to 30 carbon atoms, such as methyl,propyl, butyl, octyl, decyl, mixed C₁₂ -C₁₈, octadecyl (including thecoco group) and alkenyl groups of from 6 to 30 carbon atoms, such as theoleyl group. The heterocyclic groups contemplated include themethylbenzotriazole group.

"Hydrocarbylene" as used hereinabove, is of essentially the same scopeas "hydrocarbyl". It specifically includes alkylene groups having 1 to30 carbon atoms as well as the benzyl group.

Of particular significance, in accordance with the present invention, isthe ability to improve the resistance to oxidation and corrosion ofoleaginous materials such as lubricating media which may comprise liquidoils, in the form of either a mineral oil or a synthetic oil, ormixtures thereof, or in the form of a grease in which any of theaforementioned oils are employed as a vehicle. In general, mineral oils,both paraffinic, naphthenic and mixtures thereof, employed as thelubricant, or grease vehicle, may be of any suitable lubricatingviscosity range, as for example, from about 45 SSU at 100° F. to about6000 SSU at 100° F., and preferably from about 50 to about 250 SSU at210° F. These oils may have viscosity indexes ranging to about 100 orhigher. Viscosity indexes from about 70 to about 95 are preferred. Theaverage molecular weights of these oils may range from about 250 toabout 800. Where the lubricant is to be employed in the form of agrease, the lubricating oil is generally employed in an amountsufficient to balance the total grease composition, after accouting forthe desired quantity of the thickening agent, and other additivecomponents to be included in the grease formulation. A wide variety ofmaterials may be employed as thickening or gelling agents. These mayinclude any of the conventional metal salts or soaps, which aredispersed in the lubricating vehicle in grease-forming quantities in anamount to impart to the resulting grease composition the desiredconsistency. Other thickening agents that may be employed in the greaseformulation may comprise the non-soap thickeners, such assurface-modified clays and silicas, aryl ureas, calcium complexes andsimilar materials. In general, grease thickeners may be employed whichdo not melt and dissolve when used at the required temperature within aparticular environment; however, in all other respects, any materialwhich is normally employed for thickening or gelling hydrocarbon fluidsfor forming grease can be used in preparing the aforementioned improvedgrease in accordance with the present invention.

In instances where synthetic oils, or synthetic oils employed as thevehicle for the grease, are desired in preference to mineral oils, or incombination therewith, various compounds of this type may besuccessfully utilized. Typical synthetic vehicles includepolyisobutylene, polybutenes, hydrogenated polydecenes, polypropyleneglycol, polyethylene glycol, trimethylol propane esters, neopentyl andpentaerythritol esters, di(2-ethylehexyl)sebacate,di(2-ethylhexyl)adipate, dibutyl phthalate, flourocarbons, silicateesters, silanes, esters of phosphorous-containing acids, liquid ureasferrocene derivatives, hydrogenated synthetic oils, chain-typepolyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituteddiphenyl ethers typified by a butyl-substituted bis(p-phenoxyphenyl)ether, phenoxy phenylethers.

It is to be understood, however, that the compositions contemplatedherein can also contain other materials. For example, corrosioninhibitors, extreme pressure agents, viscosity index improvers, pourdepressants, detergants, dispersants, coantioxidants, antiwear agentsand the like can be used, including but not limited to phenates,sulfonates, succinimides, zinc dialkyl dithiophosphates,polymethacylates, olefin copolymers, and the like. These materials donot detract from the value of the compositions of this invention, ratherthe materials serve to impart their customary properties to beparticular compositions in which they are incorporated.

Mineral oil heat exchange fluids particularly contemplated in accordancewith the present invention have the following characteristics: highthermal stability, high initial boiling point, low viscosity, highheat-carrying ability and low corrosion tendency.

Further, the transmission fluids of consequence to the present inventionare blends of highly refined petroleum base oils combined with VIimprovers, detergents, defoamants and special additives to providecontrolled-friction or lubricity characteristics. Varied transmissiondesign concepts have led to the need for fluids with markedly differentfrictional characteristics, so that a single fluid cannot satisfy allrequirements. The fluids intended for use in passenger car andlight-duty truck automatic transmissions are defined in the ASTMResearch Report D-2; RR 1005 on "Automatic Transmission Fluid/PowerTransmission Fluid Property and Performance Definitions." Specificationsfor low-temperature and aircraft fluids are defined in U.S. GovernmentSpecification MIL-H-5606A.

In addition, the oxidation and corrosion resistance of functional fluidssuch as hydraulic fluids can be improved by the adducts of the presentinvention.

The fuels that may be used for the purposes of this invention include(1) liquid hydrocarbon fuel, such as diesel oil, fuel oil and gasoline,(2) alcohol fuels such as methanal and ethanol and (3) mixtures thereof.

In general, the reaction products of the present invention may beemployed in any amount which is effective for imparting the desireddegree of friction reduction or antiwear activity. In many applications,however, the product is effectively employed in amounts from about 0.1%to about 10% by weight, and preferably from about 1% to about 5% of thetotal weight of the composition.

The following Examples will present illustrations of the invention. Theyare illustrative only, and are not meant to limit the invention.

EXAMPLE 1 Synthesis of p-sulfobenzyl-N-alkyl-N,N-dimethyl ammonium innersalt

A 2 liter round bottom flask was equipped with an overhead stirrer,Barrett trap, condenser and drying tube, thermometer, and nitrogenbleed. Approximately 109 g of benzalkonium chlorides (obtainedcommercially having C₁₂ to C₁₈ alkyl with C₁₅ average) and 750 g ofethylene dichloride were charged to the flask. 100 cc of solvent wasremoved by distillation to eliminate trace H₂ O impurity. Then 278 g ofchlorosulfonic acid was added to the reaction dropwise with the reactiontemperature maintained at 25° C. After addition, the temperature wasraised to 58° C., and the reaction proceeded for 24 hours. The reactionwas chilled in an ice bath, and 250 cc H₂ O was added dropwise. Aqueoussodium hydroxide (50%) was added slowly until a pH of 7 was obtainedusing a pH meter. 95% ethanol was added and all solvents were removed byvacuum distillation. The resulting dark brown residue was stirred inwarm acetone, filtered, and allowed to sit overnight. The acetonesolution was filtered through diatomaceous earth. Solvent was removed byvacuum distillation yielding a reddish-brown viscous oil.

EXAMPLE 2 Synthesis of p-sulfobenzyl-N,N-di-hydrogenated-tallow-N-methylammonium inner salt

205 g of N,N-dihydrogenated-tallow-N-methyl amine and 50 g of benzylchloride were heated at 95°-100° C. for 15 hours to yieldN,N-dihydrogenated-tallow-N-methylbenzyl ammonium chloride, a waxy,pale-yellow solid. Then 100 g of this benzyl ammonium chloride wascharged to a 1 liter round bottom flask equipped with overhead stirrer,thermometer, and N₂ bleed. 400 cc dry ethylene dichloride was added, and109 g of chlorosulfonic acid was added dropwise over a 21/2 hour periodwith the reaction temperature held at 20°-25° C. Reaction was allowed toproceed at 52° C. for 20 hours. The reaction solution was chilled in anice bath and water was added dropwise followed by 6N NaOH. The pH wasadjusted to 7, and all solvents were removed by vacuum distillation.Toluene was added, insoluble salts were removed by filtration, andtoluene was removed from the filtrate by vacuum distillation. Theresidue was dissolved in acetone and allowed to sit overnight. A slightprecipitate was filtered, and acetone was removed by vacuum distillationto yield a dark brown oil.

EXAMPLE 3 Synthesis of p-sulfobenzyl-N,N-dicoco-N-methyl ammonium innersalt

196 g of N,N-dicoco-N-methyl amine and 61 g of benzyl chloride wereheated at 100° C. for 15 hours to yield N,N-dicoco-N-methyl benzylammonium chloride, a waxy, pale yellow solid. Then 100 g of the benzylammonium chloride was charged to a 1 liter flask equipped with overheadstirrer, thermometer, and N₂ bleed. 500 cc dry ethylene dichloride wasadded, and 128 g of chlorosulfonic acid was added dropwise over a 21/2hour period with the reaction temperature held at 20°-25° C. Reactionwas allowed to proceed at 52° C. for 20 hours. The reaction was chilledin an ice bath, and water was added dropwise, followed by 6N NaOH. ThepH was adjusted to 7, and all solvents were removed by vacuumdistillation. Toluene was added, insoluble salts were removed byfiltration, and toluene was removed from the filtrate by vacuumdistillation. The residue was dissolved in acetone and the resultingslight precipitate was filtered. Acetone was removed from the filtrateto yield a dark brown oil.

EXAMPLE 4 Synthesis of sodium 4-chloro-1-butane sulfate

A 1 liter round bottom flask was equipped with an overhead stirrer,thermometer, condenser and addition funnel with N₂ inlet. 101 g of4-chlorobutanol and 200 cc dry chloroform were charged to the flask andchilled to -30° C. 141 g of chlorosulfonic acid was added dropwise withthe reaction being allowed to warm to 0° C. during addition. Reactionwas allowed to warm to room temperature and stir for 1 hour. Thereaction solution was chilled again to -20° C., and 300 cc chilledmethanol was added followed by 104 g of 50% NaOH. Reaction was allowedto warm to room temperature, and precipitated solids were filtered anddiscarded. Filtrate was stripped free of solvents, and toluene was addedand distilled to azeotrope water in the solution. The resulting crudetan viscous solid was filtered free of salts after refluxing inmethanol. Methanol was concentrated, and the white crystalline product,sodium 4-chloro-1-butane sulfate, crystallized and was filtered.

EXAMPLE 5 Synthesis ofN-(4-sulfatobutyl)-N,N-dioleyl-N-(3-methylbenzotriazole)ammonium innersalt

23 g of sodium 4-chloro-1-butane sulfate, prepared as described inExample 4, and N,N-dioleyl-N-(3-methylbenzotriazole)amine were refluxedin 400 cc n-butanol for 41 hours. n-Butanol was removed by vacuumdistillation. The residue was dissolved in 95% ethanol, and the pH wasadjusted to 10. The resulting ppt was filtered, and the solvent removedby vacuum distillation. The dark brown filtrate was dissolved intoluene. Insoluble salts were filtered over diatomaceous earth andtoluene was removed from the filtrate by vacuum distillation to yield adark brown oil.

EXAMPLE 6 Synthesis of N-(4-sulfato butyl)-N,N-dicoco-N-methyl ammoniuminner salt

25 g of sodium 4-chloro-1-butane sulfate, prepared as described inExample 4, and 48 g of N,N-dicoco-N-methyl amine were refluxed at 106°C. in 400 cc n-butanol for 42 hours. n-Butanol was removed by vacuumdistillation. The residue was dissolved in 95% ethanol, and the pH wasadjusted to 10. After the alcohol was removed by distillation, theresulting residue was dissolved in toluene and filtered throughdiatomaceous earth. Vacuum distillation of toluene from the filtrateyielded an off-white, waxy solid product.

EXAMPLE 7 Synthesis of sodium 2-chloroethane sulfate

A 2 liter round bottom flask was equipped with an overhead stirrer,thermometer, condenser and addition funnel with N₂ lnlet. 216 g of2-chloroethanol and 550 cc of dry chloroform were charged to the flaskand chilled to -30° C. Chlorosulfonic acid was added dropwise in onehour, and the reaction was allowed to warm to room temperature and stirfor 11/2 hours. With the reaction solution again at -30° C., coldmethanol was added dropwise followed by 300 g of 50% NaOH solution. Thereaction was heated to reflux and filtered hot. The filtratecrystallized upon standing yielding white crystals, which were filteredand washed with cold methanol to yield sodium 2-chloroethane sulfate.

EXAMPLE 8 Synthesis of N-(2-sulfatoethyl)-N,N-dimethyl-N-(3-phenylstearamidopropyl)ammonium inner salt

Approximately 250 g of phenyl stearic acid and 100 g ofN,N-dimethylpropylene diamine were refluxed in 400 cc of xylene at 143°to 147° C. until all water formed in the reaction had been removed viaazeotropic distillation. The reaction solution was filtered throughdiatomaceous earth. Xylene and excess amine were removed from thefiltrate by vacuum distillation to yield a clear, brown liquid product.The 100 g of this 3-phenyl stearylamidopropylamine and 38 g of sodium2-chloroethane sulfate, prepared as described in Example 7, wererefluxed in 500 cc of n-butanol at 110° C. for 72 hours. The reactionsolution was filtered, and solvent was removed from the filtrate byvacuum distillation. The residue was dissolved in 95% ethanol, and thepH was adjusted to 10.3. Solvent was removed, and the residue wasdissolved in 800 cc of hot toluene and filtered. Removal of toluene fromthe filtrate via vacuum distillation yielded a viscous orange-brownproduct.

EXAMPLE 9 Synthesis ofN-(2-sulfatoethyl)-N,N-dimethyl-N-(3-oleamidopropyl)ammonium inner salt

Approximately 390 g of oleic acid and 278 g of N,N-dimethylpropylenediamine were refluxed in 1000 cc of xylene at 136° to 143° C. until allwater formed in the reaction had been removed via azeotropicdistillation. The reaction solution was filtered through diatomaceousearth. Xylene and excess amine were removed from the filtrate by vacuumdistillation to yield a clear, brown liquid product. Then, 81 g of this3-oleamidopropylamine and 38 g of sodium 2-chloroethane sulfate,prepared as described in Example 7, were refluxed in 500 cc of n-butanolat 110° C. for 53 hours. The reaction solution was filtered, and somesolvent was removed by vacuum distillation. 95% ethanol was added, thepH was adjusted to 11, and solvents were removed by distillation. Theresidue was dissolved in 600 cc of warm toluene and filtered throughdiatomoceous earth. Toluene was removed from the filtrate by vacuumdistillation to yield a dark brown fluid product.

EXAMPLE 10 Synthesis of N-(2-sulfatoethyl)-N,N-dicoco-N-methyl ammoniuminner salt

Approximately 103 g of N,N-dicoco-N-methyl amine and 48 g of sodium2-chloroethane sulfate, prepared as described in Example 7, wererefluxed in 800 cc of n-butanol at 110° C. for 50 hours. Solvent wasremoved by vacuum distillation. The residue was dissolved in 800 cc 90%ethanol, and the pH was adjusted to 10. Solvent was removed, and theresidue was dissolved in aqueous isopropanol and extracted withpetroleum ether. The petroleum ether layer was dried over Na₂ SO₄.MgSO₄,filtered, and stripped free of solvent. The resulting product was aviscous, white, waxy solid.

EXAMPLE 11 Synthesis of N-(2-sulfatoethyl)-N,N-dimethyl-N-oleyl ammoniuminner salt

Approximately 159 g of N,N-dimethyl-N-oleyl amine and 2-chloroethanolwere heated at 85° C. for 51/2 hours. Excess 2-chloroethanol was removedby vacuum distillatin to yield a viscous, orange, waxy solid. Then, 103g of this N,N-dimethyl-N-(2-hydroxyethyl)-N-oleyl ammonium chloride wasdissolved in 800 cc dry chloroform and chilled to 0° C. 44 g ofchlorosulfonic acid was added dropwise in 45 min. The reaction mixturewas stirred at room temperature for 2 hours, rechilled to 0° C., andquenched with 800 cc methanol. The reaction was neutralized to pH 7,filtered, and stripped free of solvents. The residue was dissolved in800 cc toluene and allowed to sit overnight. A fine white precipitatewas filtered, and toluene was removed from the filtrate via vacuumdistillation. The residue was dissolved in 50:50 hexane:toluene andfiltered. Solvents were removed from the filtrate by distillation toyield a viscous orange-brown, waxy solid.

EVALUATION OF THE COMPOUNDS

The compounds were evaluatad in a low velocity Friction Apparatus (LVFA)in a fully formulated 5W-30 synthetic automotive engine oil containing apackage including antioxidant, dispersant and detergent and having thefollowing general characteristics:

Viscosity @ 100° C.--11.0

Viscosity @ 40° C.--58.2

Viscosity Index--172

This oil is referred to as the base oil. The test compound was 1, 2 and4% of the total weight of oil.

Description

The Low Velocity Friction Apparatus (LVFA) is used to measure thecoefficient of friction of test lubricants under various loads,temperatures, and sliding speeds. The LVFA consists of a flat SAE 1020steel surface (diameter 1.5 in.) which is attached to a drive shaft androtated over a stationary, raised, narrow ringed SAE 1020 steel surface(area 0.08 in.²). Both surfaces are submerged in the test lubricant.Friction between the steel surfaces is measured as a function of thesliding speed at a lubricant temperature of 250° F. The friction betweenthe rubbing surfaces is measured using a torque arm-strain gauge system.The strain gauge output, which is calibrated to be equal to thecoefficient of friction, is fed to the Y axis of an X-Y plotter. Thespeed signal from the tachometer-generator is fed to the X-axis. Tominimize external friction, the piston is supported by an air bearing.The normal force loading the rubbing surfaces is regulated by airpressure on the bottom of the piston. The drive system consists of aninfinitely variable-speed hydraulic transmission driven by a 1/2 HPelectric motor. To vary the sliding speed, the output speed of thetransmission is regulated by a lever-cammotor arrangement.

Procedure

The rubbing surfaces and 12-13 ml of test lubricants are placed on theLVFA. A 240 psi load is applied, and the sliding speed is maintained at40 fpm at ambient temperature for a few minutes. A plot of coefficintsof friction (U_(k)) vs. speed were taken at 240, 300, 400, and 500 psi.Freshly polished steel specimens are used for each run. The surface ofthe steel is parallel ground to 4 to 8 microinches. The results in Table1 refer to percent reduction in friction compared to the unmodified oil.That is, the formulation mentioned above was tested without the compoundof this invention and this became the basis for comparison. The resultswere obtained at 250° F. and 500 psi.

                  TABLE 1                                                         ______________________________________                                        Evaluation of Friction Reducing Characteristics                                                      % Change in Coefficient                                Medium and                                                                             Additive      of Friction @                                          Additive Conc., Wt. %  5 Ft./Min.                                                                              30 Ft./Min.                                  ______________________________________                                        Base Oil --             0         0                                           Example 1                                                                              2             23        20                                           Example 2                                                                              4             17        14                                           Example 3                                                                              4             25        22                                           Example 5                                                                              4             12        13                                           Example 6                                                                              4             29        18                                           Example 8                                                                              4             18        16                                           Example 9                                                                              4             31        21                                                    2             26        23                                                    1             19        11                                           Example 10                                                                             2             21        18                                           Example 11                                                                             2             32        23                                                    1             25        19                                           ______________________________________                                    

Representative samples of the above prepared compositions were alsoevaluated for antioxidant properties with a catalytic oxidation test.Samples of 200" solvent paraffinic neutral mineral lubricating oil wereplaced in an oven at 325° F. Present in the samples were the followingmetals, either known to catalyze organic oxidation or commonly usedmaterials of construction:

a. 15.6 sq. in. of sand-blasted iron wire

b. 0.78 sq. in. of polished copper wire

c. 0.87 sq. in. of polished aluminum wire

d. 0.167 sq. in. of polished lead surface.

Dry air was passed through the sample at a rate of about 5 liters perhour for 40 hours. Table 2 shows the data.

                  TABLE 2                                                         ______________________________________                                        Catalytic Oxidation Test                                                      40 Hours @325° F.                                                                                % Increase in                                       Medium  Additive Lead     Viscosity of                                                                              Neut.                                   and     Conc.    Loss,    Oxidized Oil                                                                              No.,                                    Additive                                                                              Wt. %    mg       Using KV @210° F.                                                                  NN                                      ______________________________________                                        Base Oil                                                                              --       -0.2     4.2         3.53                                    Example 1                                                                             2        -0.03    5.5         2.62                                    Example 3                                                                             2        -0.7     5.4         2.62                                    Example 9                                                                             4        -0.6     3.7         2.85                                            2        -0.08    5.0         2.82                                    Example 11                                                                            2        -0.4     3.0         3.17                                    ______________________________________                                    

These products were non-corrosive to copper as measured in 200" solventparaffinic neutral lubricating oil using the ASTM D130-80 Copper StripCorrosivity Test. This is shown in Table 3.

                  TABLE 3                                                         ______________________________________                                        Copper Strip Corrosivity                                                      Medium  Additive   Test Rating                                                and     Conc.      ASTM D130-80                                                                              ASTM D130-80                                   Additive                                                                              Wt. %      3 Hrs. @250° F.                                                                    6 Hrs. @210° F.                         ______________________________________                                        Base Oil           1A          1A                                             Example 1                                                                             2          1A          1A                                             Example 3                                                                             2          1A          1A                                             Example 9                                                                             4          1A          1B                                             Example 10                                                                            2          1A          1A                                             ______________________________________                                    

It is apparent from the above data that the products of this inventionare effective in a variety of uses. That is, they reduce friction andthereby help to decrease fuel consumption, they are effectiveantioxidants and they are not corrosive to copper.

We claim:
 1. A composition of the formula ##STR4## wherein: (1) R⁴ is aC₁ to C₃₀ hydrocarbyl group,(2) R⁵ is a C₂ to C₄ alkyl group, (3) R¹ andR² are C₁ to C₃₀ hydrocarbyl groups, (4) R³ is a C₂ to C₆ alkylene groupor a benzyl group and (5) Q is a sulfonate or sulfate group.
 2. Thecompound of claim 1 wherein the hydrocarbyl groups are alkyl, alkenyl,aryl, aralkyl and alkaryl groups.
 3. The compound of claim 2 wherein thehydrocarbyl groups are alkyl groups.
 4. The compound of claim 3 whereinthe hydrocarbyl group is an alkenyl group of 6 to 30 carbon atoms. 5.The compound of claim 1 having the formula ##STR5##
 6. The compound ofclaim 1 having the formula ##STR6##
 7. A lubricant compositioncomprising a major proportion of a lubricating oil or grease therefromand a friction reducing amount of the formula ##STR7## wherein: (1) R⁴is a C₁ to C₃₀ hydrocarbyl group,(2) R⁵ is a C₂ to C₄ alkyl group, (3)R¹ and R² are C₁ to C₃₀ hydrocarbyl groups, (4) R³ is a C₂ to C₆alkylene group or a benzyl group and (5) Q is a sulfonate or sulfategroup.
 8. The composition of claim 1 wherein the hydrocarbyl groups arealkyl, alkenyl, aryl, aralkyl and alkaryl groups.
 9. The composition ofclaim 8 wherein the hydrocarbyl groups are alkyl groups.
 10. Thecomposition of claim 9 wherein the hydrocarbyl group is an alkenyl groupof 6 to 30 carbon atoms.
 11. The composition of claim 7 wherein thecompound has the formula: ##STR8##
 12. The compositon of claim 7 whereinthe compound has the formula: ##STR9##
 13. A compound of claim 1 whereinthe alkyl group is methyl, propyl, butyl, octyl, decyl, mixed C₁₂ -C₁₈or octadecyl.
 14. The composition of claim 2 wherein the alkyl group ismethyl, propyl, butyl, octyl, decyl, mixed C₁₂ -C₁₈ or octadecyl. 15.The composition of claim 2, 8, 9, 10, 11 or 12 wherein the lubricant isa lubricating oil.
 16. The composition of claim 15 wherein thelubricating oil is (1) a mineral oil, (2) a synthetic oil or mixturesthereof or (3) a mixture of 1 and
 2. 17. The composition of claim 15wherein the lubricating oil is a mineral oil.
 18. The composition ofclaim 15 wherein the lubricating oil is a synthetic oil or mixtures ofsynthetic oils.
 19. The composition of claim 7 wherein the lubricant isa grease.